Recyclable rhodium-catalyzed C-H activation/[4+2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight
文献类型：期刊论文
| 作者 | Meng, Haifang5; Xu, Huiying2,3; Zhou, Zhi2,3; Tang, Zhenhao5; Li, Yidi1,4; Zhou, Yu1,4 ; Yi, Wei2,3; Wu, Xiaowei1,4,5
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| 刊名 | GREEN CHEMISTRY
 |
| 出版日期 | 2022-08-11 |
| 页码 | 10 |
| ISSN号 | 1463-9262 |
| DOI | 10.1039/d2gc02347d |
| 通讯作者 | Zhou, Yu() ; Yi, Wei(yiwei@gzhmu.edu.cn) ; Wu, Xiaowei(wuxiaowei@simm.ac.cn) |
| 英文摘要 | C-H activation provides a straightforward approach to construct new chemical bonds and privileged heterocycles. However, due to common deficiencies, C-H activation still faces a great challenge towards sustainability and applications. Described herein is a robust and convenient rhodium-catalyzed regioselective C-H activation/[4 + 2] annulation for the synthesis of isoquinolones with salient features including a recyclable catalytic reaction system, unique regioselectivity, gram-scale synthesis with low catalyst loading (e.g., 0.5 mol%), ethanol as the green solvent, air and water compatibility, and simple purification processes. The roles of the hydroxy group and the pivaloyl part in both substrates, the additional pivotal function of propargyl alcohol partners, and the origin of the unique chemoselectivity are clarified based on integrated experimental and DFT studies. Additionally, a propargyl alcohol-connected distinctive hydrogen bonding network with the hydroxy group and the pivaloyl part is also rationally deduced for conferring the observed reverse regioselectivity by subsequent IGMH analysis. |
| WOS关键词 | RHODIUM(III)-CATALYZED INTRAMOLECULAR ANNULATION ; BIOMASS-DERIVED SOLVENTS ; BOND FUNCTIONALIZATION ; OXIDATIVE ANNULATION ; PROPARGYL ALCOHOLS ; AROMATIC AMIDES ; DIRECTING GROUP ; ISOQUINOLONE SYNTHESIS ; GREEN CHEMISTRY ; N-ALKYL |
| 资助项目 | Shanghai Pujiang Program[21PJ1415800] ; Guangdong Basic and Applied Basic Research Foundation[2021A1515110468] ; Natural Science Foundation of Guangdong Province[2019A1515010935] ; High-level New R&D Institute of Department of Science and Technology of Guangdong Province[2019B090904008] ; High-level Innovative Research Institute of Department of Science and Technology of Guangdong Province[2021B0909050003] ; NSFC[21877020] ; NSFC[22007020] |
| WOS研究方向 | Chemistry ; Science & Technology - Other Topics |
| 语种 | 英语 |
| WOS记录号 | WOS:000847473100001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/302114]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Zhou, Yu; Yi, Wei; Wu, Xiaowei |
| 作者单位 | 1.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China 2.Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China 3.Guangzhou Med Univ, Sch Pharmaceut Sci, Guangzhou Municipal & Guangdong Prov Key Lab Prot, State Key Lab Resp Dis, Guangzhou 511436, Guangdong, Peoples R China 4.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Dev Ctr, Shanghai 201203, Peoples R China 5.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China |
| 推荐引用方式 GB/T 7714 | Meng, Haifang,Xu, Huiying,Zhou, Zhi,et al. Recyclable rhodium-catalyzed C-H activation/[4+2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight[J]. GREEN CHEMISTRY,2022:10. |
| APA | Meng, Haifang.,Xu, Huiying.,Zhou, Zhi.,Tang, Zhenhao.,Li, Yidi.,...&Wu, Xiaowei.(2022).Recyclable rhodium-catalyzed C-H activation/[4+2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight.GREEN CHEMISTRY,10. |
| MLA | Meng, Haifang,et al."Recyclable rhodium-catalyzed C-H activation/[4+2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight".GREEN CHEMISTRY (2022):10. |
入库方式： OAI收割
来源：上海药物研究所
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